Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D207/36—Oxygen or sulfur atoms
  • C07D207/40—2,5-Pyrrolidine-diones
  • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
  • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
  • C07D207/412—Acyclic radicals containing more than six carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
  • C10M105/10—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/027—Neutral salts thereof
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/086—Imides
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/28—Amides; Imides
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/046—Overbasedsulfonic acid salts
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/045—Metal containing thio derivatives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/047—Thioderivatives not containing metallic elements
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/02—Groups 1 or 11
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/12—Groups 6 or 16
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/14—Group 7
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/16—Groups 8, 9, or 10
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/10—Semi-solids; greasy

Definitions

• This invention relates to succinimides of aminoaryl sulfonic acid metal or ammonium salts.
• this invention relates to succinimides of these salts in lubricant compositions.
• hydrocarbyl succinimides of aminoaryl sulfonic acid salts are effective multifunctional additives for lubricating oils and other organic fluids used for hydraulic purposes.
• the basic structure of these products are believed to be as follows: ##STR1##
• R is hydrocarbyl or substituted hydrocarbyl;
• X is metal or HNR' 3 and R' is hydrogen or organo or both;
• a is an integer of 1 or 2 and h is an integer up to 4;
• Ar is any aromatic-nucleus containing radical; and
• v is from 1 up to the valence of X.
• succinimide derivatives of ammonium or metal salts of amino-aryl sulfonic acid are prepared by reacting alkenylsuccinic acid anhydride or ester with the said metal or ammonium salt.
• the preparation of the alkenylsuccinic compound is generally known (U.S. Pat. Nos. 2,568,876 and 3,219,666). Essentially, this preparation involves the reaction between 1-olefin and maleic anhydride or with halosuccinic acid or anhydride or ester. The resulting product produces by addition the corresponding alkenylsuccinic compound.
• the alkenyl group may contain from 5 to 1000 carbon atoms and preferably from 30 to 500, for use in lubricants or other hydraulic fluids.
• the olefins used for preparing the alkenylsuccinic reactant in this invention include octene-1, decene-1, dodecene-1, tetradecene-1, eicosene-1, docosene-1, and the like, as well as the branched isomers thereof, and also the dimers, trimers, and higher polymers of olefins commencing with propylene, including polypropylene, polybutene, polyisobutylene, polyamylene, and the dimers, trimers, tetramers and higher polymers of hexene, octene, decene, dodecene, tetradecene, etc.
• the alkenyl group may be hydrogenated to the alkyl to produce alkylsuccinic anhydrides also useful in this invention.
• aminoaryl sulfonic acid salts which are reacted with the hydrocarbyl succinic compound have the following formula: ##STR2## in which X is ammonium, organoammonium, or a metal of Groups I, II, VI, VII, or VIII of the Periodic Table; a is an integer of 1 or 2, h is an integer of 1, 2, 3 or 4 and v is ordinarily the valence of X, and Ar is an aromatic group.
• Ar may be phenyl, naphthalene, diphenyl, dinaphthalene, phenylene naphthalene, anthracene radicals, aromatic rings bridged by methylene, methylethylene, 2,2-dimethylpropylene, oxygen, and sulfur, and these said aromatic radicals containing other substituents such as halo, hydroxy, and alkyl groups of from 1 to about 20 carbon atoms.
• Ar contains more than one nucleus the sulfonate and amino groups may be on the same ring or different rings.
• a is 1 and h is 1 or 2 and X is an alkali metal or alkaline earth metal or a metal of group IIB or ammonium, HNR' 3 wherein R' is alkyl or aminoalkyl or poly(aminoalkyl) of from 1 to 20 carbon atoms or hydrogen or both.
• R' is alkyl or aminoalkyl or poly(aminoalkyl) of from 1 to 20 carbon atoms or hydrogen or both.
• metals sodium, lithium, potassium, calcium, magnesium, barium, strontium and zinc are the preferred.
• aminoaryl sulfonic acid salts regardless of the number or position of groups on the nucleus or nuclei, may also be referred to hereinafter as "sulfanilates.”
• the salts of this invention may range from simple monomolecular structures to complicated high molecular weight gel structures. If the aminoaryl sulfonic acid reactant contains one or more of each amino, sulfonic, or hydroxy group on the ring or rings, but the metal is monovalent, the product is a monomolecular or limited molecular weight salt. However, if the metal is polyvalent, (1) with a single amino group and sulfo group, the product is a "v-mer", that is, the number of attached aminoaryl sulfonic acid groups is the valence of the metal; (2) with more than one amino or sulfo group, then crosslinked polymeric products could result.
• One method of obtaining the salts of this invention involves reaction between the hydrocarbyl succinic acid, anhydride or ester and an ammonium sulfonate (of orthanilic acid, metanilic acid or sulfanilic acid): ##STR3##
• This reaction may be carried out at a temperature in the range of from about 75° C. to about 300° C. and preferably from about 90° C. to about 180° C.
• a temperature in the range of from about 75° C. to about 300° C. and preferably from about 90° C. to about 180° C.
• polar or nonpolar solvents may be used whenever desired.
• solvents as hexane, dioxane, and other alkanes, aromatics, ketenes, aldehydes, dimethylacetamide, dimethylformamide and the like may be used. Reaction is continued until water of condensation removed indicates imide formation.
• the resulting succinimide of the ammonium sulfanilate may then be reacted, if desired, with a metal compound, replacing the ammonium group with metal.
• a metal compound replacing the ammonium group with metal.
• metal compounds as hydroxides, carbonates, bicarbonates, oxides, acetates, formates, propionates and the like may be used.
• a stoichiometric balance of reactants is preferred, that is, one equivalent of sulfonic group per equivalent of metal. However, excess of one reactant may be present.
• the ammonium salts themselves have useful detergent properties in lubricant compositions. They are also the preferred precursor in preparing the metal salts because of their availability and ease in producing an ionic aminoaryl sulfonic acid salt initially.
• an ammonium sulfanilate may first be reacted with the metal reagent prior to forming the succinimide.
• the metal sulfanilate may be reacted with the hydrocarbyl succinic compound to yield the corresponding metal-containing succinimide.
• Monovalent metal products are understood to have the structure ##STR4## and divalent metal products ##STR5##
• the metal sulfanilates may also be obtained by reacting the metal reagent with sulfanilic acid directly. This route is also within the scope of this invention. Reaction with the hydrocarbyl succinic compound may be carried out at the aforementioned temperatures.
• a polar solvent may be used for the reaction between the metal sulfanilate and the hydrocarbyl succinic compound, e.g. ethers, alcohols, esters and amides.
• a preferred solvent is the N-(lower alkyl)amides, such as dimethylformamide and dimethylacetamide.
• aminoaryl sulfonic acid salt reactants of this invention are a species of a genus consisting of one or more aromatic rings, amino groups and sulfonic acid groups.
• higher molecular weight, or polymeric, succinimides are available which may provide enhanced viscosity controls for industrial fluids.
• the final succinimide structure may be ##STR6## using sodium as the metal for illustration purposes.
• the disulfanilic salt may be reacted with the alkenylsuccinic compound at a 1:2 mole ratio.
• X being ammonium or monovalent metals, the above structure is understood to result.
• succinimido-sulfanilate groups may be present in the molecule.
• R group may contain up to 1000 carbon atoms
• products of this invention may have molecular weights of over 100,000. It is speculated that polymeric structures of such products may be as follows (HSI representing the hydrocarbyl succinimido moiety) using magnesium as a typical metal: ##STR7## the dangling valences being attached to further sulfonic acid groups.
• a suggested generic formula for the repeating section of this polymer could be ##STR8##
• the reaction between amino di(aryl sulfonic) salts and the hydrocarbyl succinic compound are carried out at the same temperatures as previous reactions; longer reaction periods may, of course, be required. Excess reactants may be present outside the stoichiometric ratio.
• a further modification of this invention is the reaction involving aminoaryl polysulfonic acid salts, especially the disulfonic salt.
• aminoaryl polysulfonic acid salts especially the disulfonic salt.
• simple compounds would be obtained with monovalent metals and ammonium; polymers may result with polyvalent metals.
• Two structures may be shown to represent these forms ##STR9## the dangling valences attached to magnesium being further linked to additional sulfonic acid groups. All such monomeric and polymeric forms are within the scope of this invention.
• additives are excellent multifunctional agents in lubricants, both liquid and grease, power transmission and heat-exchange fluids and the like media. Additive properties of these agents of particular interest are the dispersant and viscosity properties. These additives are also useful in preventing suspensoids in fluid from settling on machine or engine surfaces thereby interfering with the operation involved. They have also been shown to possess antioxidant properties as well.
• oils containing certain of these additives evidence unusual film-forming characteristics under high shear. While, commercial viscosity index improvers often cannot sustain the high initial VI (which they are employed to provide) under shear, the additives of this invention permit the oil to retain initial VI to an unexpectedly greater extent. Moreover, the film thickness of the oil compositions of this invention actually increases under temporary high shear forces in certain instances, while normally a film is thinner or even disrupted. Such properties make this family of additives unique.
• the additives may be used with the other well-known additives common for industrial use, such as other detergent-dispersants, VI improvers, antioxidants, anti-rust agents and the like.
• additives common for industrial use, such as other detergent-dispersants, VI improvers, antioxidants, anti-rust agents and the like.
• Such compounds as the ashless succinimides of amines and amine-metal complexes, phosphorodithioates, phenates, neutral and overbased sulfonates and the like may be present in the fluid compositions of this invention.
• the triethylammonium sulfanilate was reacted on an equimolar basis with alkenylsuccinic anhydride derived from the following olefins: (2) polybutene of 640 molecular weight, (3) normal octadecene, (4) iso-octadecene, and (5) polybutene of 1400 molecular weight.
• the reaction mixtures were heated at 165° C. under nitrogen for 2 hours in each case.
• Example 10 The reaction of Example 10 was repeated with different metal reactants:
• Magnesium sulfanilate was prepared by reacting magnesium carbonate with sulfanilic acid in a mole ratio of 1:2 by heating to remove water and carbon dioxide.
• the trimethylammonium salt was reacted with LiOH.H 2 O at 165° C. overnight to produce 1108 grams of the lithium salt corresponding to the ammonium salt of Example 26.
• the tetraethylene pentamine salt of 1,6-aminonaphthalene sulfonic acid was prepared by mixing the two reactants together in equimolar amount at a temperature of 180° C. for a period of 2 hours.
• the resulting ammonium salt was then reacted with the succinic anhydride of Example 28.
• a calcium salt of 1,4,2-aminophenol sulfonic acid is reacted with the succinic anhydride of Example 1.
• the resulting product is the calcium salt of the alkenylsuccinimide of 1,4,2-aminophenol sulfonic acid.
• Example 16 The Mg sulfanilate of Example 16 was reacted with an alkenylsuccinic anhydride in which the alkenyl group is derived from an olefin having of molecular weight of about 157. The resulting product is the corresponding succinimide of the magnesium salt.
• a magnesium salt was prepared by reacting the magnesium salt of disulfonic acid with the succinic anhydride of Example 1 at a mole ratio of 1:2 salt to anhydride.
• a similar product was obtained by reacting the product of Example 24 with magnesium carbonate.
• SA alkenyl group molecular weight
• ANS aminonaphthalene sulfonic acid salt
• DS disulfanilic acid salt
• ADS aniline disulfonic acid salt
• APS sulfonic acid salt of 1,4,2-aminophenol sulfonic acid salt
• NDS aminonaphthalene disulfonic acid salt
• the products of this invention evidence excellent dispersant, antioxidant and viscosity index properties in such organic fluids as lubricating oils. The following tests are used to evaluate such properties:
• Preparation of the carbon black dispersion to prepare the bed initially involves mixing 12.5 mg of 0.18 micron diameter carbon black in 50 grams of white oil and subjecting the same to ultrasonic radiation at 80kc/sec. for 15 minutes.
• Sludge determinations were conducted by mixing the oxidized oil (30 grams) with 300 ml hexane, stirring overnight, and filtering through a medium frit glass filter (10 to 15 microns).
• the concentration of additive in the test lubricant sample is 2.04% by weight in a solvent-refined mineral oil stock of 100 SS (at 100° F.).
• Oil compositions containing the products of this invention are measured for viscosity index and increase in thickening (viscosity increase per weight percent).

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• Emergency Medicine (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Lubricants (AREA)

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• 1974
  • 1974-08-16 GB GB3618174A patent/GB1457049A/en not_active Expired
  • 1974-08-20 AU AU72534/74A patent/AU7253474A/en not_active Expired
  • 1974-08-21 NL NL7411165A patent/NL7411165A/xx unknown
  • 1974-08-23 FR FR7429045A patent/FR2241568A1/fr not_active Withdrawn
  • 1974-08-23 DE DE2440523A patent/DE2440523A1/de active Pending
• 1975
  • 1975-11-24 US US05/634,812 patent/US4053425A/en not_active Expired - Lifetime

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